Perfumery mixture



Patented Aug. 6, 1940 UNETEC STA'E'Efi Parent orricr PERFUREERY MIXTURENo Drawing. Application January 15, 1940, Se-

rial No. 313,971. In Germany December 9,

4 Claims.

The present invention relates to perfumery mixtures.

U. S. Patent No. 2,169,984 relates to perfumery mixtures which arecharacterized by the fact 5 that on preparing them there aresimultaneously used ,ketals derived from pyrocatechol which contain inthe ketone residue at least 6 aliphatica-lly bound carbon atoms.

I have now found that the ketals which are 10 produced from thehomologues of pyrocatechol may likewise be used for the preparation ofperfumery mixtures; in this case it is not necessary that in the ketoneresidue at least 6 carbon atoms are present. Whereas ketals derived fromunsubstituted pyrocatechol and containing less than 5 carbon atoms areuseless, since theypossess too low, a boiling point and have ahydrocarbonlike odor, for instance, the odor of toluene, the ketalsprepared, for instance, from acetone and an alkyl pyrocatechol have asufficiently high boiling point and constitute already distinctlyvaluable perfumery compounds. These bodies are obtained by causing alkylsubstituted or cyclo-alkyl substituted pyrocatechols to react in knownmanner with ketone or by introducing into the nucleus of pyrocatecholketals alkyl groups or cyclo-alkyl groups. These compounds maysuccessfully be used as a substitute of natural amber in appropria emixtures; furthermore, by altering the side chains and the ketone theremay be prepared bodies having the most varied odors. Besides bodies ofan amber-like odor compounds may, for instance, be obtained which havethe odor of genuine opoponax or-labdanum. In the following table aseries of bodies of that kind is enumerated by way of example:

Tertiary butyl pyrocatechol dimethyl ketal boiling at 112 C. to 115 C.under a pressure of 4 to 5 mm.

Isohexyl--pyrocatechol-dimethyl-ketal boiling at 122 C. to 125 C. undera pressure of 4 mm.

Tertiary butyl-pyrocatechol-methylethyl-ketal boiling at 120 C. to 122C. under a pressure of 4 mm.

Isohexyl-pyrocatechol-methylethyl-ketal boiling at 125 C. to 128 C.under a pressure of 4 mm.

Cyclopentyl-pyrocatechol-dimethyl-ketal boiling at 120 C. to 123 C.under a pressure of 4 to 5 mm.

Tertiary butyl=pyrocatechol-cyclotetramethylene-ketal boiling at 140 C.to 145 C. under a pressure of 4 mm.

Isopropyl-pyrocatechol-methylethyl-ketal boiling at 105 C. to 108 C.under a pressure of 4 to 5 mm. a

The following examples serve to illustrate the invention, but they arenot intended to limit it thereto;- the parts being by weight:

Example I 400 parts of phosphorus pentoxide are intro- 5 duced in thecourse of 4 to 6 hours into a mixture of 400 parts of tertiarybutyl-pyrocatechol and parts of acetone; 200 parts'of acetone aresimultaneously added drop by drop. On treating and washing the mixturewith lye the non- 10 transformed tertiary butyl-pyrocatechol isdissolved; it may be recovered from the solution. By a distillation ofthe crude oil there are obtained 250 to 300 parts of tertiarybutyl-pyrocatechol-dimethyl-ketal boiling at 112 C. to 15 C. under apressure of 4 to 5 mm.

Example II 5 parts of boron trifluoride are added to a mixture of 200parts of pyrocatechol-dimethyl-ketal and 100 parts of isohexylene; thesolution is al- 'lowed to stand for 24 hours or for some days.

Example 1.-Fougre-mixture Parts 35 Linalyl acetate Coumarim 150 Anlsylacetate 65 Lavender oil 300 Vetiver oil 60 40 Tarragon oil 10- Bergamotoil East-Indian sandalwood oil, 40 Benzyl acetate 25 Methyl ionone 1 0045 Mousse de chene (absol.) 50 Patchouli 40 Musk ketone 50 Geranium oil50 Jasmin (absol.) 20 50 Salicylic acid isobutyl ester 50 Benzoeresinoid 50 Tertiary butyl-pyrocatechol-cyclotetra methylene ketal l 60Example 2.-Russian leather perfume Parts Parts Bergamot oil 270East-Indian sandalwood oil 180 iasmm 35 avender oil 10 Bergamot oil- 200t i 30 Vetiver oil 50 n 70 Geranium 011 180 ang-y Birch tar, rectifieda. 20 f 'i' r" f "i'g' Z3 Benzoic acid methyl ester 20 ISO exy pyroca e00 nne y e Sallicylic acid methyl ester 20 m Salicylic acid amyl ester 80t I claim is: ffi g i g 3 g 1. Perfumes containing as a constituent aketal Linaloe on 80 derived from a pyrocatechol of the generalCirclopentyl-pyrocatechol-dimethy1ketal--- 30 formula 0H 1000 R- Ezample3.Ch1mre (Cyprus) 0H Parts 7 Santalol 60 wherein R means a substituentof the group con- Coumarin- I 20 sisting of alkyl radicles andcycloalkyl radicl'es, Musk ketone 50 and 01 a ketonic compound of thegroup consist- Labdanum (absoL) ing of aliphatic ketones andcycloaikanones. Tarragon oil 2. Perfumes containing as a constituentterti- Sage oil 30 ary butylpyrocatecholdimethylketal. Vetiver oil 60 3.Perfumes containing as a constituent terti- Linalool 30 arybutyipyrocatechohnethylethylketal. Patchouli n 20 4. Perfumes containingas'a constituent hexyl- Iso-eugenol pyrocatecholdimethylketal. Methylionone V Mousse de chne (absoL) ALBERT WEISSENBORN.

